Synthesis of higher sugars as precursors for the synthesis of chiral polyhydroxylated macrocyclic lactones

A general method for the synthesis of higher sugars that can be used as precursors for the synthesis of polyhydroxylated macrocyclic lactones (macrolides) was described. The extension of the carbohydrate chain of a hexopyranose was effected at its C(6) hydroxymethyl carbon by coupling of...

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Main Authors:	Miljković Momčilo, Habash-Marino Margaret
Format:	Article
Language:	English
Published:	Serbian Chemical Society 2000-01-01
Series:	Journal of the Serbian Chemical Society
Subjects:	higher sugars sugar chain elongation wittig reaction sugar phosphoniumsalts polyhydroxylated macrocyclic lactones
Online Access:	http://www.doiserbia.nb.rs/img/doi/0352-5139/2000/0352-51390007497M.pdf

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spelling	doaj-861b0d1a156d47608dde784d7cdaee232020-12-18T07:43:48ZengSerbian Chemical Society Journal of the Serbian Chemical Society0352-51391820-74212000-01-0165749750510.2298/JSC0007497M0352-51390007497MSynthesis of higher sugars as precursors for the synthesis of chiral polyhydroxylated macrocyclic lactonesMiljković Momčilo0Habash-Marino Margaret1The Pennsylvania State University, The Milton S. Hershey Medical Center, Department of Biochemistry and Molecular Biology, Hershey, USAThe Pennsylvania State University, The Milton S. Hershey Medical Center, Department of Biochemistry and Molecular Biology, Hershey, USAA general method for the synthesis of higher sugars that can be used as precursors for the synthesis of polyhydroxylated macrocyclic lactones (macrolides) was described. The extension of the carbohydrate chain of a hexopyranose was effected at its C(6) hydroxymethyl carbon by coupling of two carbohydrate precursors via Wittig reaction. In this way 6,7-dideoxy-2,3,4,5,8,9,10-hepta-O-methyl-11-O-triphenylmethyl-D-arabino-D-glucoundecanose diethyl dithioacetal (1) was synthesized as a model compound.http://www.doiserbia.nb.rs/img/doi/0352-5139/2000/0352-51390007497M.pdfhigher sugarssugar chain elongationwittig reactionsugar phosphoniumsaltspolyhydroxylated macrocyclic lactones
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Miljković Momčilo Habash-Marino Margaret
spellingShingle	Miljković Momčilo Habash-Marino Margaret Synthesis of higher sugars as precursors for the synthesis of chiral polyhydroxylated macrocyclic lactones Journal of the Serbian Chemical Society higher sugars sugar chain elongation wittig reaction sugar phosphoniumsalts polyhydroxylated macrocyclic lactones
author_facet	Miljković Momčilo Habash-Marino Margaret
author_sort	Miljković Momčilo
title	Synthesis of higher sugars as precursors for the synthesis of chiral polyhydroxylated macrocyclic lactones
title_short	Synthesis of higher sugars as precursors for the synthesis of chiral polyhydroxylated macrocyclic lactones
title_full	Synthesis of higher sugars as precursors for the synthesis of chiral polyhydroxylated macrocyclic lactones
title_fullStr	Synthesis of higher sugars as precursors for the synthesis of chiral polyhydroxylated macrocyclic lactones
title_full_unstemmed	Synthesis of higher sugars as precursors for the synthesis of chiral polyhydroxylated macrocyclic lactones
title_sort	synthesis of higher sugars as precursors for the synthesis of chiral polyhydroxylated macrocyclic lactones
publisher	Serbian Chemical Society
series	Journal of the Serbian Chemical Society
issn	0352-5139 1820-7421
publishDate	2000-01-01
description	A general method for the synthesis of higher sugars that can be used as precursors for the synthesis of polyhydroxylated macrocyclic lactones (macrolides) was described. The extension of the carbohydrate chain of a hexopyranose was effected at its C(6) hydroxymethyl carbon by coupling of two carbohydrate precursors via Wittig reaction. In this way 6,7-dideoxy-2,3,4,5,8,9,10-hepta-O-methyl-11-O-triphenylmethyl-D-arabino-D-glucoundecanose diethyl dithioacetal (1) was synthesized as a model compound.
topic	higher sugars sugar chain elongation wittig reaction sugar phosphoniumsalts polyhydroxylated macrocyclic lactones
url	http://www.doiserbia.nb.rs/img/doi/0352-5139/2000/0352-51390007497M.pdf
work_keys_str_mv	AT miljkovicmomcilo synthesisofhighersugarsasprecursorsforthesynthesisofchiralpolyhydroxylatedmacrocycliclactones AT habashmarinomargaret synthesisofhighersugarsasprecursorsforthesynthesisofchiralpolyhydroxylatedmacrocycliclactones
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Synthesis of higher sugars as precursors for the synthesis of chiral polyhydroxylated macrocyclic lactones

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